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chlorotetrolic acid synthesis
- Product Name:chlorotetrolic acid
- CAS Number:13280-03-0
- Molecular formula:C4H3ClO2
- Molecular Weight:118.52
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Yield: 60%
Reaction Conditions:
Stage #1:2-propynyl chloride with n-butyllithium in tetrahydrofuran at -78;
Stage #2: with carbon dioxide in tetrahydrofuran at -78; for 2 h;Acidic aqueous solution;
Steps:
Example 15; 4-Chloro-but-2-yanoic acid
Propargyl chloride (2 mL, 26.84mmol) was dissolved in 40 mL of tetrahydrofuran under nitrogen and cooled to -78C. After addition of n-butyllithium (5.4 mL, 13.42mmol, 2.5 M in n-hexane) and stirred for 15 min, a stream of dry carbon dioxide was passed through it at -78C for two hours. The reaction solution was filtered and neutralized with 3.5 mL of 10% sulfuric acid. After evaporation of the solution, the residue was extracted with ether. The ether solution was washed with saturated brine solution, and dried over sodium sulfate. After evaporation of the dry ether solution, 0.957g (60%) of an oil product was obtained: ESMS m/z 116.6 (M-H+).
References:
Wyeth Holdings Corporation EP1117659, 2003, B1 Location in patent:Page 51
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